Benzoyl Peroxide → Methyl 2-bromo-2-(3-fluoro-4-methoxyphenyl)acetate

HRID 76859노트

반응식

HRID 76859 반응식
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([F:13])[CH:6]=1.C1C(=O)N([Br:22])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[CH:4]([Br:22])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([F:13])[CH:6]=1

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14897830Methyl 2-(3-fluoro-4-methoxyphenyl)acetate

생성물 1

HCID 58827055Methyl 2-bromo-2-(3-fluoro-4-methoxyphenyl)acetate

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

The (3-fluoro-4-methoxyphenyl)acetic acid methyl ester (5.16 g, 26.0 mmol) is dissolved in carbon tetrachloride (300 mL) along with NBS (5.56 g, 31.3 mmol) and benzoyl peroxide (0.63 g, 2.60 mmol) and refluxed for 2 h. The solution is then allowed to cool to room temperature and is filtered. The filtrate is evaporated and the residue purified via flash column chromatography (EtOAc/hexanes 5:95→EtOAc/hexanes 2:8) to give bromo-(3-fluoro-4-methoxyphenyl)acetic acid methyl ester as a yellow oil. 1H NMR (CDCl3) δ 7.37 (d, J=12 Hz, 1H), 7.26-7.23 (m, 1H), 6.93 (t, J=8 Hz, 1H), 5.31 (s, 1H), 3.91 (s, 3H), 3.81 s, 3H).

후처리

  1. temperaturerefluxed for 2 h
  2. filtrationis filtered
  3. customThe filtrate is evaporated
  4. customthe residue purified via flash column chromatography (EtOAc/hexanes 5:95→EtOAc/hexanes 2:8)

출처 및 근거

ORD 기록
ord-8a8c369710e54f858ac57f4c90a8b9a2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835646B2

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